Water → HCID 12149006, compound

HRID 1007563Notes

Reaction equation

HRID 1007563 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][N:8]=2)[N:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[C:3]=1[C:21]#[N:22].[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][SH:31].[F-].[Cs+].O>CS(C)=O>[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:30][S:31][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][N:8]=2)[N:5]=[C:4]([C:17]([F:20])([F:19])[F:18])[C:3]=1[C:21]#[N:22]

Participants

6

Reactant 4

HCID 962WaterHCID 25953Cesium fluorideHCID 5221752-Fluorobenzyl mercaptanHCID 12135150HCID 12135150, compound

Product 1

HCID 12149006HCID 12149006, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

5-Chloro-1-(5-methanesulfonyl-pyridin-2-yl)-3-trifluoromethyl-1H-pyrazole-4-carbonitrile (0.512 g, 1.46 mmol) and (2-fluoro-phenyl)-methanethiol (0.415 g, 2.92 mmol) were dissolved in dry DMSO (5 ml) and cesium fluoride (0.154 g, 2.92 mmol) was added to the clear solution. The resulting mixture was stirred at 20° for a period of 48 hours. Analytical HPLC indicated the reaction completion. The reaction mixture was poured into water (50 ml) and the resulting mixture was extracted with ethyl acetate (20 ml). The organic extract was dried over magnesium sulfate and concentrated with a rotary evaporator. The desired product (0.55 g, 83%) was isolated by chromatography on silica gel eluting with a gradient (from 20-40%) of ethyl acetate in hexane. MS: 457, r.t.: 27, 1H-NMR (CDCl3, 400 MHZ) δ 9.05 (d, 1H, H—Ar), 8.44-8.41 (q, 1H, H—Ar), 8.05 (d, 1H, H—Ar), 7.34-7.27 (m, 2H, H—Ar), 7.13-7.02 (m, 2H, H—Ar), 4.61 (s, 2H, CH2 of the benzyl group), 3.16 (s, 3H, CH3 of the CH3SO2 group) ppm.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate (20 ml)
  2. extractionThe organic extract
  3. dry with materialwas dried over magnesium sulfate
  4. concentrationconcentrated with a rotary evaporator

Sources & evidence

ORD record
ord-f76e2f1e91d94fd895fe1bd01b3ab47c
Source dataset
uspto-grants-2004_09
Patent number
US06794512B2

Reaction notes

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